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Regioselective synthesis of isoxazole and 1,2,4-oxadiazole-derived phosphonates via [3 + 2] cycloaddition

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Abstract

The results of the study on reactions of halogenoximes bearing (protected) functional groups or fluorinated substituents with various phosphorus-containing dipolarophiles are described. To control the regioselectivity of the reaction, vinylphosphonates bearing a leaving group (i.e. bromine or dialkylamino group) in the α or β position were used; 3,5- and 3,4-disubstituted isoxazoles were obtained in 47–80% and 63–75% yields, respectively. The reaction was also effective for the parent vinyl phosphonate and cyanophosphonate; in this case, the corresponding isoxazoline- and 1,2,4-oxadiazole-derived phosphonates were isolated in 55–69% and 34–73% yields, respectively. The utility of the products obtained was demonstrated by the preparation of direct conformationally restricted analogues of phosphohistidine.

Graphical abstract: Regioselective synthesis of isoxazole and 1,2,4-oxadiazole-derived phosphonates via [3 + 2] cycloaddition

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Publication details

The article was received on 12 Sep 2018, accepted on 01 Oct 2018 and first published on 01 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02257G
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Regioselective synthesis of isoxazole and 1,2,4-oxadiazole-derived phosphonates via [3 + 2] cycloaddition

    B. A. Chalyk, A. S. Sosedko, D. M. Volochnyuk, A. A. Tolmachev, K. S. Gavrilenko, O. S. Liashuk and O. O. Grygorenko, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02257G

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